Letters from the Old World

Letters from the Old World

The Myth of “Comfort”

Why you feel worse in “comfortable” clothes…

Evan Amato's avatar
Evan Amato
Jan 23, 2026
∙ Paid
Take it from Cary Grant: comfort and style are not mutually exclusive.

Ask anyone why it is that people don’t dress well anymore, and the answer you get back usually boils down to one thing: comfort.

Modern slovenliness, it appears, is solely the result of man’s desire to be comfortable. Contemporary clothing is just so soft and cozy that a suit and tie could never compete with the latest athleisure quarter-zip! Although this premise is flawed (I will explain why later in this article), its sentiment is widespread. But none of that matter, because it’s not actually the real cause of today’s problems.

No, what most people miss is that the reason we dress so poorly today is not because we desire comfort, but because we don’t know what comfort truly is. In other words, it’s not about fabric, but philosophy. Most people’s idea of comfort only takes into account one aspect of what the concept really means. Coincidentally, this is why you often feel worse when you wear “comfortable” clothes.

Today, I want to help you explore some of the painfully overlooked elements of comfort. We’ll start out with philosophy, and then move towards practical advice on how to dress with style without abandoning comfort in the process.

My goal is to give you the tools you need to know what comfort really is, so you can be comfortable in everything you wear. Because after all, if you can’t dress comfortably, you can’t dress well…


Our mission here at Letters from the Old World is to share the secrets of Old World elegance, and our approach is two-fold:

1) Every Wednesday, we send a free article exploring the theology and philosophy of why beauty matters, particularly in regards to decor and dress.

2) Every Friday, we send What’s In a Fit, a members-only article exploring practical tips and guidelines for dressing well.

If this resonates with you, then subscribe below to join the aesthetic renaissance.


What’s In a Word

Comfort is strength, Mr. Bond…

To kick things off, let’s start by looking at the word “comfort” itself. It derives from the Latin confortare, which combines con- (an intensifying prefix which in this case means “thoroughly/fully”) with fortis (”strong”). Its original meaning was something closer to fortify, in the sense of “to bring strength to”.

In Old French, the meaning of the word “comfort” shifted more towards a sense of consolation, or providing support in grief. Only in the 17th century did it first take on connotations of physical ease. Today, it could be argued that the word entails something closer to gluttony than it does to the mere absence of physical discomfort.

So even though the word has evolved over time, parts of its earliest meaning still remain. All it takes is a little thought experiment to see how.

For example, if you’re home alone over the weekend and want to watch a movie, what do you wear? What’s most comfortable? Now, what about if your company’s CEO invites you to a shareholder dinner at a fancy downtown restaurant. What kind of clothes would make you feel most comfortable then? The same ones?

Here we see the original Latin meaning creeping back in: at the shareholder dinner, to be “comfortable” means something far more expansive than the optimization of your physical comfort. It means dressing like you belong with the other people in the room and not feeling out of place. It means wearing clothes that give you confidence and energy. It means, in other words, something that brings strength to you: con + fortis.

This is the first step in reframing what comfort truly is. Far greater than mere physical comfort, it is something that brings consolation to both your psyche and your soul…


A Fish Out of Water?

The great Frank drinking alone

Now at this point, someone might object by saying that when they dress well, they feel out of place, since no one else in their environment does so and they stand out. They might also add that they feel inauthentic, and thus psychologically uncomfortable. Does this not mean that for them, dressing well is inherently uncomfortable?

The key to resolving this perceived dilemma is to add a long-term perspective to your understanding of comfort. Just as going to the gym for the first time can be intimidating, you do so because it is ultimately good for you in the long run. Yes, you feel out of place, like you don’t belong. You’re not sure if you’re doing the exercises properly, or even which workout routine you should be following. The “authentic you” is the person who doesn’t go to the gym, and who prefers the comforts of home.

Yet if you were to allow this “authentic you” to remain always in the comforts of home, you would sooner or later grow exceedingly uncomfortable. Weight issues or illnesses stemming from a lack of physical activity would soon infringe on your life and cause you daily discomfort. Your decision to tolerate the short-term discomforts of the gym, therefore, is based on your desire for long-term comfort and health.

Even Arnold was a beginner in the gym at one point. (Nice suspenders, by the way)

The same goes for when you begin to put in effort to how you dress. Sure, you’ll feel a bit out of place and will make some mistakes here and there. You’ll feel the discomfort of being a beginner and of having to learn by doing. But does this mean that you’re “inauthentic”? By no means! It simply means you’re undergoing the normal process of growth.

If anything, to not grow and face discomfort is the perhaps most inauthentic thing you can do, since humans are made to grow, and discomfort is part of growth. Or, in the words of Saint Paul, “when I was a child, I spoke like a child, I thought like a child, I reasoned like a child. When I became a man, I gave up childish ways.” It is indeed a good thing to grow up and shed your childish forms of dress.

All this to say, however, the pursuit of comfort is not in and of itself a bad thing. Because if you have the right understanding of comfort, you’ll realize that the most “comfortable” path in the long-term often requires the most friction and discomfort in the present. But how much friction should you realistically expect? Is it true, as the Italians say, that non c’è bellezza senza dolore — “there’s no beauty without pain”?

Contrary to popular belief, dressing well doesn’t have to be uncomfortable. In the next sections, I break down practical tips for ensuring that comfort and style go hand in hand as you start to dress more seriously.

Because when it comes to feeling good while dressing well, one simple rule is the key to it all…

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